The Journal of Organic Chemistry

Stereochemical control in cyclofunctionalization of olefinic alcohols and olefinic phenols with benzeneselenenyl chloride

AG Schultz, P Sundararaman

Index: Schultz, Arthur G.; Sundararaman, Padmanabhan Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2455 - 2462

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Citation Number: 5

Abstract

Olefinic alcohols 8a-c are prepared from condensations of the lithium enolate derived from y- butyrolactone (5) with cyclohexanone, 4-methylcyclohexanone, and 4, 4- dimethylcyclohexanone to give lactonic alcohols 6a-c, followed by dehydration with phosphorous pentoxide and Celite to give cyclohexenes 7a-c and lactone saponification and esterification with diazomethane; dehydration of 6b gives 7b as an equimolar mixture ...